Sulfuric acid magnesium salt (1:1) → Benzyl 5-acetyl-4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyridine-3-carboxylate

HRID 420645Notes

Reaction equation

HRID 420645 reaction equation
[C:1]([CH:4]([C:38](=O)[CH3:39])[CH:5]([C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1)[CH:6]([C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)=[O:18])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:3])[CH3:2].S([O-])([O-])(=O)=O.[Mg+2]>C(O)C>[C:1]([C:4]1[CH:5]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)[CH:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C:17](=[O:18])[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:29])[F:27])[CH:21]=2)[C:38]=1[CH3:39])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 59666215Benzyl 4-acetyl-3-(4-cyanophenyl)-5-oxo-2-({[3-(trifluoromethyl)phenyl]amino}carbonyl)hexanoate

Product 1

HCID 59666193Benzyl 5-acetyl-4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of benzyl 4-acetyl-3-(4-cyanophenyl)-5-oxo-2-({[3-(trifluoromethyl)phenyl]amino}carbonyl)hexanoate (7.5 g, 15.6 mmol) (Example 5A), anhydrous magnesium sulfate (15 g, 125 mmol) and Amberlyst 15® (7.5 g) in ethanol (300 ml) is stirred overnight at reflux. The reaction is cooled to room temperature, filtered through a pad of celite and concentrated in vacuo. The residue is purified by flash chromatography over silica gel 60 with cyclohexane/ethyl acetate mixtures as eluent.

Workup

  1. temperatureat reflux
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by flash chromatography over silica gel 60 with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-88e04c6600ad4294b197896fbdedd866
Source dataset
uspto-grants-2012_01
Patent number
US08097629B2

Reaction notes

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